This dissertation is a close comparative analysis of two landmark texts of self-writing. The first, the Confessions of Augustine of Hippo, presents a narrative of his early life until a fundamental shift occurs in his conversion scene. No longer the young pear thief, the author describes taking up and reading the text of Paul in a dramatic scene. In the second part of the text, the bishop of Hippo exegetes passages of Scripture. The second Confessions of Jean-Jacques Rousseau portray the lamentations of a maligned philosophe, recounting the tale of his young life in obscurity and the miseries of his life as a public figure. While defying the audience to judge him, he details the adventures of his life in order to preserve an accurate portrait of himself against the one circulating in the public sphere. Under the Foucauldian analytic framework attending to the relations between power, truth, and subject, the comparison of the two texts illuminates the notion of the confession they helped to create, and well as the critical questions that can be brought to bear on the confession. The comparison takes parallel scenes to examine the confession staged in each. In the first chapter, I compare the notion of subjugation put into place in each text through their retellings of the Genesis scene. In the second chapter, the scenes of sexual desire and the juridical configure the relationship between the ethical and epistemological axes of their task. The breaks in the middle of each text reflect the way the confession structures the text and the story of the transformation of each author in chapter three. In the last two chapters, I compare the function of the public and the function of textual exercises in the two compositions. In chapter 4, I examine the way each text portrays the reception of the text and the effects of the text on its reader. In chapter 5, I examine the reading and writing practices folded into the Confessions of each author. Over the course of the comparisons, I raise the truth-telling practice of confession as a crucial and central theme to understand the composition, operation, and significance of these two canonical texts. The Foucauldian lens help to deploy the confession as an analytic framework across historical and epistemological shifts, as well as bring their political stakes into view. In turn, the comparison raises a domain of rhetorical and political questions for contemporary discourse and lasting practices of confession. This analysis inflects the significance of these two texts for philosophical, literary, and theological investigations through the emphasis on the relationship between the ethical, political, and epistemological axes of their confessions.